
Holiday rentals with outdoor seating in Winthrop
Find and book unique Holiday Houses with Outdoor Seating on Airbnb
Top-rated Holiday Houses with Outdoor Seating in Winthrop
Guests agree: These Holiday Houses with Outdoor Seating are highly rated for location, cleanliness and more.

Off-Grid Escape. Wood Fired Hot Tub, Snowshoes
Relax at this off-grid modern A-Frame cabin on 90 acres in Maine's Lakes Region. The cabin is tucked deep in the woods, far away from everything. 4 kayaks and firewood included. Separate bunk cabin increases sleeping capacity to 10 Wood-Fired Cedar Hot Tub - a relaxing, very unique experience 5+ lakes nearby- excellent swimming and kayaking Cedar throughout cabin, concrete countertops, cedar/concrete shower. Outdoor firepit. Hiking trails. Beaver Pond. Property has private airstrip (51ME)

Room B with private entrance, bathroom & hot tub
Room B is a small (10’ x 10’) but cozy room with full size bed with luxury mattress and private bathroom (5’ x8’) with towel warmer & glass shower. The room includes a desk, TV, minifridge, microwave, coffee maker, dresser, reading chair & private entrance. In the summer we have bicycles to use on the rail trail and kayaks for the Kennebec River. Year round hot tub. Downtown is just a block away where there are numerous restaurants and pubs with live music. Hiking trails & waterfalls nearby.

Welcome to The Nest - 1 bed, deck w/bath & parking
Enjoy easy access to entertainment, restaurants & shopping. Historic Cumstom Theater, local Bakery, Bar & pizzeria. Willows Awake and The Vista wedding venues w/tasting rooms. Microbrewery’s Grateful Grains & Van der Brew tap rooms w/food trucks & entertainment. Maine turnpike access for shopping;Freeport LLBean, Portland, Bath, Augusta, Hallowell & Lew/Auburn areas. Tour Bates,Bowdoin, Colby, Thomas & Husson. Golfing, boating, antiques, State Parks, hiking/walking trails,beaches & Festivals.

1820s Maine Cottage with Garden
Enjoy a cozy shipbuilder's cottage in Bath, Maine. This quaint apartment attached to a family home has its own entrance and contains a bedroom, a bathroom, a kitchen, and a living room with antique details that reflect its 200-year old history. Only a 15-minute walk to historic downtown Bath, a 3-minute drive to Thorne Head Preserve, and a 25-minute drive to Reid State Park and Popham Beach. Come appreciate everything MidCoast Maine has to offer! PLEASE NOTE: This apartment has steep stairs!

SUMMER ROSE a Yurt for ALL Seasons
SUMMER ROSE - Overlooking the Field of Dreams pasture, and future pond, is a spacious wooden yurt with a spectacular ceiling, personal hot tub and "Hideout" a screened in sanctuary. The Appleton Retreat is situated on 120 acres of privately owned land. To the south, a short walk from Summer Rose, is the Pettengill Stream, a resource protected area where you can view wildlife or kayak; and to the north, a wooded trail leads to a secluded pond on 1,300 acres of Nature Conservancy protected land.

Maine lakehouse-Ice fishing, skiing, snowmobiling
Beautiful lake living & winter activities, 2.5 hours from Boston, 40 min. from Portland. Near skiing- 1:20 from Sunday River, 1:10 Pleasant Mtn., 1:05 Mount Abram Ski Area, 0:20 Lost Valley. This cozy 2-bedroom home on Lake Sabattus with 110 feet of private lake frontage, sleeps four. All the amenities of home incl. a SS kitchen with newer appliances. Minutes to Lewiston/Auburn - close to dining and stores. Well known ice fishing spot , cross-country skiing nearby too. Fire pit, great sunsets.

Forest Bathing: Off-Grid Tiny Home, Pond w/ Kayak
Immerse yourself in our forest and serene pond. Quiet 40-acre commune consists of two tiny house cabins + barn on private pond. Book one of the simple yet elegant cabins/barn for more guests. Modern, off-grid, solar-powered retreat. Two solid glass walls to bring you closer to nature while staying in our simple yet elegant tiny house with all comforts of home. 5 min walk to shared fire pits, kayaks, pond & seasonal picnic shelter. AWD SUV or truck required. Off-grid, so no A/C. Pet fee $89.

Modern Hideaway in Augusta
Centrally located modern guest home in Augusta, access points to Portland, Midcoast Maine, and Bangor. Spacious master bedroom with closet, additional bedroom, both bedrooms with queen size beds. Handicap bathroom equipped with grab rail and also handicap accessible shower with sit down bench. Many brand new amenities. 55 inch TV has Roku with access to Netflix , Disney Plus, and more! Strong WiFi with the ability to work remotely if needed and explore Augusta and surrounding area.

The cottage at Marble Farm.
This beautiful private cottage is the perfect place to unwind after a long day of adventure! New, bright and comfortable, this secluded cottage is conveniently located just 40 minutes from Sugarloaf, 50 minutes from Saddleback and 10 minutes to downtown Farmington. Feel free to walk, fat bike or x-country ski on nearly 4 miles of groomed private trails located just outside your front door! Contains a full kitchen for meal prep, as well as high speed internet, and climate control.

Cozy log cabin on private pond, near Reid St Park!
Winter or summer, the Little River Retreat will help you step away from the world - but still be minutes from Reid State Park, Five Islands Lobster, the Georgetown General Store, and the rugged beauty of Midcoast Maine. This is our family camp, with our own books, games, and “vibe”. It is not a hotel, and some things may not be “industry standard”. We love the unique charm of this space and place, and many repeat guests do too. We hope you will treasure (and care for it) as we do!

The Maine Frame | Modern A-Frame Cabin in Freeport
• Perfect for small families or couples, our signature A-Frame cabin features a modern interior gas burning fireplace, soaring ceilings, huge windows, stylish interiors, and all the comforts of home. • This cozy 1,100 square foot space comfortably accommodates up to four guests in two bedrooms (one with a King-size bed and the other with a Queen-size bed) and a shared bathroom. • 7 minute drive to downtown Freeport. • Proud to be ranked in the top 1% and voted Guest Favorite!

Hallowell Hilltop Home with Hot Tub & Sauna
Discover this newly renovated 2-bedroom, 1-bathroom home in a quiet family-friendly neighborhood in Hallowell. This home's rustic-modern design, natural light, and all-new amenities make it a perfect getaway. Relax in the hot tub, grill on the deck, enjoy the backyard or visit downtown Hallowell and explore its restaurants, cafes, live music and antique shops. This home is also minutes away from several hiking and walking trails that can all be found in our guidebook.
Popular amenities for Winthrop outdoor seating rentals
Holiday House Rentals with Outdoor Seating

Farmington and UMF! Walk to town! Skiers welcomed!

Sunny 2-BR 5 min to Bates & River Trails

1830s Cape hosted by George & Paul

Historic Maine Farmhouse - The Harding Farm

The Nifty Village House

Riverside

Moore's place

Private Lake House, Firepit & Amazing Sunset Views
Apartment rentals with outdoor seating

Harborview - Curated East End Escape w/ Parking

Serenity, Privacy, Clean and Bright

Cape Elizabeth Garden Apt+Beach+Close to Portland!

Oceanside Open Concept 2BR- East End/ Downtown

Downtown Hideaway-Loft HotTub Modern Clean Private

Skiers Get-Away (1 BR near AT - w/views)

Cozy SoPo Condo

Harbor for Two
Condo rentals with outdoor seating

Charming, newly remodeled space atop Munjoy Hill.

Modern Industrial Beach Cottage

Cozy condo by the beach!

Top Of The Line Stay!

Direct Ocean View on the Eastern Promenade

Comfy condo with loft by the beach!

Slope Side | Ground floor | Hot Tub, Pool, Sauna

Sunday River Locke Mountain Ski In/ Ski Out Pool
Quick stats about holiday rentals with outdoor seating in Winthrop

Total holiday rentals
Explore 40 holiday rentals in Winthrop

Nightly prices starting at
Winthrop holiday rentals start at $66 NZD per night before taxes and fees

Verified guest reviews
Over 1,250 verified reviews to help you choose

Family-friendly holiday rentals
30 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wi-Fi availability
40 of Winthrop holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wi-Fi and Pool across Winthrop rentals

4.9 Average rating
Winthrop stays are highly rated by guests—averaging 4.9 out of 5!
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- Rentals with outdoor seating Kennebec County
- Rentals with outdoor seating Maine
- Rentals with outdoor seating United States
- Sebago Lake
- Sunday River Resort
- Popham Beach, Phippsburg
- Popham Beach State Park
- Pemaquid Beach
- Willard Beach
- East End Beach
- Pemaquid Point Lighthouse
- Coastal Maine Botanical Gardens
- Wolfe's Neck Woods State Park
- The Camden Snow Bowl
- Pleasant Mountain Ski Area
- Maine Maritime Museum
- Bradbury Mountain State Park
- Mt. Abram
- Farnsworth Art Museum
- Portland Museum of Art
- Rockland Breakwater Light
- Sunday River
- Grafton Notch State Park
- Pineland Farms
- Maine Mineral & Gem Museum
- Bug Light Park
- East End Beach




